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Updated: Jul 9, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Direct Access to Sulfonamidated-1,4-Benzoquinones via Sulfonamidation of Aryl Alcohol-Derived Quinone Monoacetals
Rahul Bangari1,2, Rudraa Singh Rajpoot1, Abhishek Patel2
1Department of Chemistry, IIT Dharwad, Permanent Campus, Chikka Malligwad, Dharwad, Karnataka 580007, India.
Abstract:
An alcohol-derived quinone monoacetal (QMA)-enabled strategy for the direct synthesis of sulfonamidated benzoquinones via a nucleophilic addition-elimination sequence using N-methoxy sulfonamides as reagents is reported. QMA serves as a uniquely competent surrogate of benzoquinone. The protocol exhibits broad substrate scope, excellent functional group tolerance, and gram-scale applicability. Mechanistic studies, supported by DFT calculations, reveal that acid-promoted acetal hydrolysis followed by tautomerization-assisted methanol elimination is the key step governing product formation.
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